Methyl iodide → 4-(1-Methoxy-1-methyl-ethyl)-benzoic acid methyl ester

HRID 855297노트

반응식

HRID 855297 반응식
[H-].[Na+].[CH3:3][O:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[CH3:17]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:3][O:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:15][CH3:17])([CH3:14])[CH3:13])=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodide2회HCID 24758Sodium hydride2회HCID 25517Ammonium ChlorideHCID 18174533Methyl 4-(2-hydroxypropan-2-yl)benzoate

생성물 1

HCID 181744854-(1-Methoxy-1-methyl-ethyl)-benzoic acid methyl ester수율 38%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

439 mg of sodium hydride (60% in mineral oil) were suspended in 10 ml DMF and a solution of 1.64 g of 4-(1-hydroxy-1-methyl-ethyl)-benzoic acid methyl ester (8.4 mmol) in 10 ml DMF was added at 0° C. The mixture was allowed to warm to rt and was stirred for 1 h at this temperature before 0.79 ml of methyl iodide (12.7 mmol) were added. After 17 h additional 338 mg of sodium hydride (60% in mineral oil) and 0.53 ml methyl iodide (8.4 mmol) were added and stirring was continued for 20 h. Then saturated ammonium chloride solution was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried with magnesium sulfate, filtered and the solvent was evaporated. Chromatographic purification (silica gel; c-hexane/EtOAc 9:1 to 4:1) of the remaining residue yielded 661 mg (38%) of 4-(1-methoxy-1-methyl-ethyl)-benzoic acid methyl ester as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 1.54 (s, 6H), 3.09 (s, 3H), 3.92 (s, 3H), 7.48 (d, J=9 Hz, 1H), 8.02 (d, J=9 Hz, 1H).

후처리

  1. additionwere added
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customChromatographic purification (silica gel; c-hexane/EtOAc 9:1 to 4:1) of the remaining residue

출처 및 근거

ORD 기록
ord-e901a7077483444fb01cdac17508e0e4
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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